Grundinformationen
- Standard-SMILES
O=c1[nH]c2ccccc2c(=O)o1- InChIKey
TXJUTRJFNRYTHH-UHFFFAOYSA-N- Summenformel
- C8H5NO3
- Durchschnittliche Molmasse
- 163,13 g/mol
- Monoisotopische Masse
- 163,02694302
Überblick
structure given in first source
Namen und Bezeichner
- Bevorzugter Name
- Isatoic Anhydride
- IUPAC
- 1H-3,1-benzoxazine-2,4-dione
- Lokaler Name
- 4H-3,1-Benzoxazin-2,4(1H)-dion
- Englischer Name
- Isatoic Anhydride
- Summenformel
- C8H5NO3
- Molmasse
- 163.13
Namen und Synonyme
Isatoic anhydride118-48-92H-3,1-Benzoxazine-2,4(1H)-dioneISATOIC ACID ANHYDRIDE4H-3,1-Benzoxazine-2,4(1H)-dioneN-Carboxyanthranilic anhydrideDTXSID60269553,1-Benzoxazine-2,4(1H)-dioneAnthranilic acid, N-carboxy-, cyclic anhydrideBenzoic acid, 2-(carboxyamino)-, cyclic anhydrideR8TFA74Y4U2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
Weitere Namen anzeigen
1H-BENZO[D][1,3]OXAZINE-2,4-DIONEIsatoic2-(carboxyamino)-benzoicacicyclicanhydrideBENZOXAZINEDIONE4H-3Isatoic Ac4(1H)-dione
1,2-dihydro-3,1-benzoxazine-2,4-dioneNSC-295551h-benz(d)(1,3)oxazine-2,4-dioneNSC-104662DTXCID9069552,4-dioxo-1,2-dihydro-4h-3,1-benzoxazineRefChem:791499204-255-0
Datenbank-Bezeichner
- CAS
118-48-9- PubChem CID
- 8359
- DTXSID
DTXSID6026955- ChEMBL
CHEMBL1235999、CHEMBL346059- UNII
- R8TFA74Y4U
- EC Number
- 204-255-0
- Nikkaji
- J5.526C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1
- Polarare Oberfläche (TPSA)
- 55,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 226
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesChemical shift
Color/Form
PRISM FROM ALC OR GLACIAL ACETIC ACID; CRYSTALS FROM ALCOHOL OR DIOXANE
TAN POWDER
SolubilityMISCIBLE IN WATER, HOT ALC, AND ACETONE; INSOL IN ETHER, BENZENE, AND CHLOROFORM
Melting Point243 °C WITH DECOMPOSITION
Physical Description
Dry Powder
Tan solid; [Hawley] Grey powder; [MSDSonline]
Physikochemische Eigenschaften
- Schmelzpunkt
- 233 °C · 233 °C (dec.) (lit.)
- Siedepunkt
- 290.19 °C · 290.19°C (rough estimate)
- Dichte
- 1 · 1,52 g/cm3
- Dampfdichte
- 5.6 · 5.6 (vs air)
- Brechungsindex
- 1.551 · 1.5510 (estimate)
- Flammpunkt
- 308 °C · 308 °C
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 0.3 g/l · 0.3g/l
- pka
- 11.06 · 11.06±0.20(Predicted)
- Aggregatzustand
- Powder
- Farbe
- Beige to brown
- Wasserlöslichkeit
- decomposes
- BRN
- 136786 · 136786
- InChI
- 1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11)
- InChIKey
- TXJUTRJFNRYTHH-UHFFFAOYSA-N
- SMILES
- O=C1Nc2ccccc2C(=O)O1
- LogP
- 0.978 · 0.978 (est)
- CAS Datenbank
- 118 · 118-48-9(CAS DataBase Reference)
- NIST chemische Informationen
- Isatoic anhydride(118-48-9)
- EPA chemische Informationen
- 2 H-3,1-Benzoxazine-2,4 · 2H-3,1-Benzoxazine-2,4(1H)-dione (118-48-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 5.2% (11 of 210) of reports.
Warning
H317 (94.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]
Gefahrenhinweise
Regulatory Information
Chemical: 2H-3,1-Benzoxazine-2,4(1H)-dione
2H-3,1-Benzoxazine-2,4(1H)-dione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-3,1-Benzoxazine-2,4(1H)-dione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.
Status: Active Update: 25-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18515
Isatoic anhydride: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn eye irritant; May cause skin sensitization; [eChemPortal: ESIS] Danger of skin sensitization; [MAK] An irritant; May cause skin sensitization; [MSDSonline] See ACID ANHYDRIDES.
Hazard Classes and Categories
Skin Sens. 1 (94.8%)
Eye irritation - category 2
Eye Irrit. 2
Toxikologische Informationen
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Non-Human Toxicity ExcerptsTESTED FOR ANTIFERTILITY EFFECTS IN MICE AFTER ORAL ADMIN FOR 21 DAYS, WITH MALES INTRODUCED @ END OF 1ST WK, & AFTER INJECTIONS TWICE DAILY FOR 5 DAYS. EFFECTIVE IN DECR NUMBER OF MICE WITH LITTERS @ LEAST 50%.
Sicherheitsdaten
- F
- 3
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29349990
- RTECS-Nr.
- DM3100000
- risk_code
- 36-43
- Toxizität
- LD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg
- hazard_code
- Xi
- safety_code
- 24-26-37
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 118-48-9(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2Skin Sens. 1
- Selbstentzündungstemperatur
- >600 °C
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationEndogenous substances and drugs that inhibit or block the activity of BETA-LACTAMASES.
Verwendung und Herstellung
Uses
Used to make polymer curing agents, anthranilic esters, heterocyclic compounds, benzyne, saccharin, methyl anthranilate, and pesticides; Also used as a corrosion inhibitor in engine lubricants and as a modifier of natural and synthetic polymers and resins; [HSDB]
Plastic Composites Manufacturing [Category: Industry]
INTERMEDIATE FOR POLYMER CURING AGENTS, ANTHRANILIC ESTERS, HETEROCYCLIC COMPD, & BENZYNE
CHEM INT FOR SACCHARIN, METHYL ANTHRANILATE, PESTICIDES (EG, GUTHION); CORROSION INHIBITOR IN ENGINE LUBRICANTS; MODIFIER OF NATURAL & SYNTHETIC POLYMERS & RESINS
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
2023: 100,000 - <250,000 lb
(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS
(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS
Industry UsesIntermediate
Methods of ManufacturingPASSING PHOSGENE INTO A SOLUTION OF ANTHRANILIC ACID IN AQUEOUS HYDROCHLORIC ACID
Formulations/PreparationsGRADE: TECHNICAL, 96% MIN
General Manufacturing Information
Not Known or Reasonably Ascertainable
2H-3,1-Benzoxazine-2,4(1H)-dione: ACTIVE
A BICYLIC MOLECULE COMPOSED OF A BENZENE RING ATTACHED @ ORTHO & META POSITIONS TO HETEROCYCLIC RING. IT FORMS USEFUL ANTHRANILIC ACID DERIVATIVES BY REACTION WITH HYDROGEN.
Anwendungen
VerwendenIsatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.
Darstellung
synthetischePhosphorus tribromide (0.035 mol) was added to a solution of N-carbethoxy- or N-carbobenzoxy-anthranilic acid (0.1 mol;prepared by coupling anthranilic acid with the corresponding carbalkoxy chloride in the usual way) in anhydrous diethyl ether (100 mL). After 24 h at room temperature, isatoic anhydride had separated as a microcrystalline product. It was collected by filtration, washed with dry diethyl ether, and recrystallized from ethanol. Yield ca. 90%.
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Ergänzende Hinweise
DefinitionA bicyclic molecule composed of a benzene ring attached at the oand mpositions to a heterocyclic ring. It forms useful anthranilic acid derivatives by reaction with hydrogen.
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